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Shortly after the United States captured Venezuelan President Nicolás Maduro in January, President Donald Trump’s administration turned its gaze to the Cuban regime. In an executive order, Trump declared a national emergency over what he called an “unusual and extraordinary threat” posed by Cuba. He accused the island nation of harboring Russian spies and welcoming terrorist groups, such as Hamas and Hezbollah.

The executive order contained a pointed threat: Countries that continue to send oil to Cuba would face punishing tariffs. Given that the United States had already halted shipments from Venezuela, the threat was directed at Cuba’s only other major oil supplier—Mexico. Trump’s efforts to choke Havana into regime change have forced Mexican President Claudia Sheinbaum into a difficult balancing act. She is now caught between a historic allegiance to Cuba and the need to placate a White House intent on expanding its power across the region at any cost.

Shortly after the United States captured Venezuelan President Nicolás Maduro in January, President Donald Trump’s administration turned its gaze to the Cuban regime. In an executive order, Trump declared a national emergency over what he called an “unusual and extraordinary threat” posed by Cuba. He accused the island nation of harboring Russian spies and welcoming terrorist groups, such as Hamas and Hezbollah.

The executive order contained a pointed threat: Countries that continue to send oil to Cuba would face punishing tariffs. Given that the United States had already halted shipments from Venezuela, the threat was directed at Cuba’s only other major oil supplier—Mexico. Trump’s efforts to choke Havana into regime change have forced Mexican President Claudia Sheinbaum into a difficult balancing act. She is now caught between a historic allegiance to Cuba and the need to placate a White House intent on expanding its power across the region at any cost.

For much of last year, Mexico sent roughly 22,000 barrels of oil per day to Cuba, though that number fell to around 7,000 barrels per day after U.S. Secretary of State Marco Rubio visited Mexico City in September. (Prior to the U.S. blockade of Venezuela, the Maduro government was averaging 35,000 barrels per day to Cuba.) By the time that Trump issued his executive order, Mexico had halted all oil shipments to Cuba, a move that Sheinbaum sought to cast as a “sovereign decision,” despite reports that the pause was out of fear of U.S. reprisals.

Despite Mexico’s pause on oil shipments, Trump upped the ante with his tariff threat, which appeared to blindside Sheinbaum. She came out swinging the next day, warning of a “humanitarian crisis” in Cuba, which already faced rolling blackouts and severe fuel shortages. Sheinbaum vowed that Mexico would “provide........

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